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288-14-2 Usage

Description

Isoxazole is a five-membered heterocyclic compound with various pharmacological actions, characterized by a monocyclic structure consisting of three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is found in some natural products and serves as the basis for a number of drugs. Isoxazoles are largely applied in pharmaceuticals and therapeutics, including insecticidal, antibacterial, antibiotic, antitumor, antifungal, antituberculosis, anticancer, and ulcerogenic properties. They also have effects on reducing blood glucose, eliminating pain, resisting inflammation, killing harmful bacteria, and controlling and reducing the risk of HIV.

Uses

Used in Pharmaceutical Industry:
Isoxazole is used as a key component in the development of various drugs, such as the COX-2 inhibitor valdecoxib and anti-inflammatory drugs, due to its diverse pharmacological actions and potential therapeutic applications.
Used in Insecticide Industry:
Isoxazole is used as a natural insecticide, acting as an inhibitor of acetylcholinesterase (AChE) and binding to the Sxcantiporter, which helps in controlling and reducing the risk of insect infestations.
Used in Antibacterial and Antifungal Applications:
Isoxazole is used as an antibacterial and antifungal agent, contributing to the development of treatments for bacterial and fungal infections.
Used in Antituberculosis and Anticancer Applications:
Isoxazole is used as an antituberculosis and anticancer agent, playing a role in the development of drugs for the treatment of tuberculosis and various types of cancer.
Used in Anti-inflammatory and Analgesic Applications:
Isoxazole is used as an anti-inflammatory and analgesic agent, helping in reducing inflammation and eliminating pain.
Used in Antiviral Applications:
Isoxazole is used in the development of antiviral drugs, particularly for controlling and reducing the risk of HIV.
Used in Beta-lactamase-resistant Antibiotics:
Isoxazole is used as a component in some beta-lactamase-resistant antibiotics, such as cloxacillin, dicloxacillin, and flucloxacillin, to enhance their effectiveness against bacterial infections.
Chemical Properties:
Isoxazole is a colorless liquid with a wide range of applications in various industries.

References

https://en.wikipedia.org/wiki/Isoxazole http://www.ijpcbs.com/files/volume3-2-2013/15.pdf

Hazard

Narcotic and psychomimetic effects.

Check Digit Verification of cas no

The CAS Registry Mumber 288-14-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,8 and 8 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 288-14:
(5*2)+(4*8)+(3*8)+(2*1)+(1*4)=72
72 % 10 = 2
So 288-14-2 is a valid CAS Registry Number.
InChI:InChI=1/C3H3NO/c1-2-4-5-3-1/h1-3H

288-14-2 Well-known Company Product Price

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  • Alfa Aesar

  • (L01607)  Isoxazole, 99%   

  • 288-14-2

  • 5g

  • 317.0CNY

  • Detail
  • Aldrich

  • (151637)  Isoxazole  99%

  • 288-14-2

  • 151637-5G

  • 351.00CNY

  • Detail
  • Aldrich

  • (151637)  Isoxazole  99%

  • 288-14-2

  • 151637-25G

  • 1,261.26CNY

  • Detail

288-14-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name isoxazole

1.2 Other means of identification

Product number -
Other names 1,2-oxazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:288-14-2 SDS

288-14-2Synthetic route

di(1,3-dioxolan-2-yl)methane
4405-17-8

di(1,3-dioxolan-2-yl)methane

ISOXAZOLE
288-14-2

ISOXAZOLE

Conditions
ConditionsYield
With hydroxylamine hydrochloride at 110 - 120℃; Green chemistry;85.5%
malondialdehyde bis(diethyl acetal)
122-31-6

malondialdehyde bis(diethyl acetal)

ISOXAZOLE
288-14-2

ISOXAZOLE

Conditions
ConditionsYield
With hydroxylamine hydrochloride In water at 70℃; for 3.5h;43%
With hydrogenchloride; water; hydroxylamine
With hydrogenchloride; hydroxylamine
With hydroxylamine hydrochloride
Trimethylsilanecarbonitrile oxide
84405-51-6

Trimethylsilanecarbonitrile oxide

acetylene
74-86-2

acetylene

ISOXAZOLE
288-14-2

ISOXAZOLE

Conditions
ConditionsYield
In tetrahydrofuran; water under 760 Torr; for 1.5h; Ambient temperature;28%
With water In tetrahydrofuran Ambient temperature; Yield given;
Propargylic aldehyde
624-67-9

Propargylic aldehyde

ISOXAZOLE
288-14-2

ISOXAZOLE

Conditions
ConditionsYield
With hydroxylamine
With hydrogenchloride; hydroxylamine
1,3,3-triethoxypropene
5444-80-4

1,3,3-triethoxypropene

ISOXAZOLE
288-14-2

ISOXAZOLE

Conditions
ConditionsYield
With hydrogenchloride; water; hydroxylamine
vinyl acetate
108-05-4

vinyl acetate

sodium cyanate
15736-98-8

sodium cyanate

ISOXAZOLE
288-14-2

ISOXAZOLE

Conditions
ConditionsYield
With sulfuric acid Erhitzen des Reaktionsprodukts mit wss. H2SO4;
3t-chloro-propenal
4643-13-4

3t-chloro-propenal

ISOXAZOLE
288-14-2

ISOXAZOLE

Conditions
ConditionsYield
With hydrogenchloride; water; hydroxylamine
acetic acid-(1-bromo-3,3-dichloro-propyl ester)
98021-69-3

acetic acid-(1-bromo-3,3-dichloro-propyl ester)

ISOXAZOLE
288-14-2

ISOXAZOLE

Conditions
ConditionsYield
With hydrogenchloride; ethanol; hydroxylamine
With hydrogenchloride; ethanol; hydroxylamine; sodium acetate
1-acetoxy-1,3,3-tribromopropane
86046-91-5

1-acetoxy-1,3,3-tribromopropane

ISOXAZOLE
288-14-2

ISOXAZOLE

Conditions
ConditionsYield
With hydrogenchloride; ethanol; hydroxylamine
With hydrogenchloride; ethanol; hydroxylamine; sodium acetate
sodium cyanate
15736-98-8

sodium cyanate

acetylene
74-86-2

acetylene

A

ISOXAZOLE
288-14-2

ISOXAZOLE

B

isoxazole-3-carbaldehyde-oxime

isoxazole-3-carbaldehyde-oxime

Conditions
ConditionsYield
With sulfuric acid
Propargylic aldehyde
624-67-9

Propargylic aldehyde

hydroxylamine
7803-49-8

hydroxylamine

ISOXAZOLE
288-14-2

ISOXAZOLE

ISOXAZOLE
288-14-2

ISOXAZOLE

3-aminoprop-2-enal
25186-34-9

3-aminoprop-2-enal

Conditions
ConditionsYield
With hydrogen; nickel In methanol at 20℃; under 2068.65 Torr;100%
With hydrogen; Raney nickel In methanol under 2068.65 Torr; for 24h; Parr apparatus;94%
With hydrogen; nickel In methanol; chloroform
ISOXAZOLE
288-14-2

ISOXAZOLE

Oxone

Oxone

3-methyl-4-(4-methylthiophenyl)-5-phenylisoxazole
219679-74-0

3-methyl-4-(4-methylthiophenyl)-5-phenylisoxazole

3-methyl-5-(4-methylsulfonylphenyl)-4-phenylisoxazole
181695-93-2

3-methyl-5-(4-methylsulfonylphenyl)-4-phenylisoxazole

Conditions
ConditionsYield
In tetrahydrofuran; methanol; water95%
ISOXAZOLE
288-14-2

ISOXAZOLE

1,5-diphenylpenta-1,4-diyn-3-ol
15814-32-1

1,5-diphenylpenta-1,4-diyn-3-ol

(Z)-1-(3-oxoprop-1-en-1-yl)-2,5-diphenyl-1H-pyrrole-3-carbaldehyde

(Z)-1-(3-oxoprop-1-en-1-yl)-2,5-diphenyl-1H-pyrrole-3-carbaldehyde

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere; chemoselective reaction;94%
ISOXAZOLE
288-14-2

ISOXAZOLE

1,5-di(thiophen-3-yl)penta-1,4-diyn-3-ol
1613231-71-2

1,5-di(thiophen-3-yl)penta-1,4-diyn-3-ol

(Z)-1-(3-oxoprop-1-en-1-yl)-2,5-di(thiophen-3-yl)-1H-pyrrole-3-carbaldehyde

(Z)-1-(3-oxoprop-1-en-1-yl)-2,5-di(thiophen-3-yl)-1H-pyrrole-3-carbaldehyde

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 5h; Inert atmosphere; chemoselective reaction;93%
ISOXAZOLE
288-14-2

ISOXAZOLE

carbon dioxide
124-38-9

carbon dioxide

isoxazole-5-carboxylic acid
21169-71-1

isoxazole-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide In tetrahydrofuran at 20℃; under 1125.11 Torr; for 0.25h;
Stage #2: ISOXAZOLE In tetrahydrofuran at 20℃; under 1125.11 Torr; for 12h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water regioselective reaction;
91%
ISOXAZOLE
288-14-2

ISOXAZOLE

1-(4-bromophenyl)-5-cyclopropylpenta-1,4-diyn-3-ol

1-(4-bromophenyl)-5-cyclopropylpenta-1,4-diyn-3-ol

(Z)-5-(4-bromophenyl)-2-cyclopropyl-1-(3-oxoprop-1-en-1-yl)-1H-pyrrole-3-carbaldehyde

(Z)-5-(4-bromophenyl)-2-cyclopropyl-1-(3-oxoprop-1-en-1-yl)-1H-pyrrole-3-carbaldehyde

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 3h; Inert atmosphere; chemoselective reaction;91%
ISOXAZOLE
288-14-2

ISOXAZOLE

(3-methoxyhexa-4,5-dien-1-yn-1-yl)benzene

(3-methoxyhexa-4,5-dien-1-yn-1-yl)benzene

C15H11NO

C15H11NO

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 14h; Reagent/catalyst;88%
ISOXAZOLE
288-14-2

ISOXAZOLE

C11H12O

C11H12O

(Z)-2,5-dicyclopropyl-1-(3-oxoprop-1-en-1-yl)-1H-pyrrole-3-carbaldehyde

(Z)-2,5-dicyclopropyl-1-(3-oxoprop-1-en-1-yl)-1H-pyrrole-3-carbaldehyde

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 7h; Inert atmosphere; chemoselective reaction;87%
ISOXAZOLE
288-14-2

ISOXAZOLE

4-methoxydeca-1,2-dien-5-yne

4-methoxydeca-1,2-dien-5-yne

C13H15NO

C13H15NO

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 20h;87%
ISOXAZOLE
288-14-2

ISOXAZOLE

2-(2-phenylethenyl)-5-methoxybenzaldehyde
223553-44-4

2-(2-phenylethenyl)-5-methoxybenzaldehyde

A

C19H13NO2

C19H13NO2

B

C19H15NO3

C19H15NO3

Conditions
ConditionsYield
With copper diacetate In toluene at 110℃; for 5h; regioselective reaction;A 87%
B 7%
ISOXAZOLE
288-14-2

ISOXAZOLE

C12(13)CH12O

C12(13)CH12O

C14(13)CH11NO

C14(13)CH11NO

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 25h;85%
ISOXAZOLE
288-14-2

ISOXAZOLE

1-(3-methoxyhexa-4,5-dien-1-yn-1-yl)-4-methylbenzene

1-(3-methoxyhexa-4,5-dien-1-yn-1-yl)-4-methylbenzene

C16H13NO

C16H13NO

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 23h;85%
ISOXAZOLE
288-14-2

ISOXAZOLE

o-(phenylethynyl)benzaldehyde
59046-72-9

o-(phenylethynyl)benzaldehyde

A

4-benzoyl-2-naphthonitrile

4-benzoyl-2-naphthonitrile

B

C18H13NO2

C18H13NO2

Conditions
ConditionsYield
With copper diacetate In toluene at 110℃; for 4h; regioselective reaction;A 85%
B 8%
ISOXAZOLE
288-14-2

ISOXAZOLE

2-[(4-chlorophenyl)ethynyl]benzaldehyde
1251832-81-1

2-[(4-chlorophenyl)ethynyl]benzaldehyde

A

C18H10ClNO

C18H10ClNO

B

C18H12ClNO2

C18H12ClNO2

Conditions
ConditionsYield
With copper diacetate In toluene at 110℃; for 3.5h; regioselective reaction;A 85%
B 8%
ISOXAZOLE
288-14-2

ISOXAZOLE

4-(3-(4-methylpiperazinyl)-1-propoxy)-5-methoxy-2-aminobenzoic acid methyl ester

4-(3-(4-methylpiperazinyl)-1-propoxy)-5-methoxy-2-aminobenzoic acid methyl ester

7-(3-(4-methylpiperazinyl)-1-propoxy)-4-one-6-methoxyquinoline-3-carbonitrile

7-(3-(4-methylpiperazinyl)-1-propoxy)-4-one-6-methoxyquinoline-3-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; for 5h;85%
ISOXAZOLE
288-14-2

ISOXAZOLE

N,4-dimethyl-N-(3-methylbut-3-en-1-yn-1-yl)benzenesulfonamide

N,4-dimethyl-N-(3-methylbut-3-en-1-yn-1-yl)benzenesulfonamide

A

C16H18N2O3S

C16H18N2O3S

B

C17H20N2O3S

C17H20N2O3S

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-2-(3H)-ylidene]gold(I)chloride; silver(I) triflimide In 1,2-dichloro-ethane at 70℃; for 4h;A 84%
B 8%
ISOXAZOLE
288-14-2

ISOXAZOLE

C17H14O

C17H14O

C19H13NO

C19H13NO

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 24h;84%
ISOXAZOLE
288-14-2

ISOXAZOLE

C13H10(2)H2O

C13H10(2)H2O

C15H9(2)H2NO

C15H9(2)H2NO

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 12h;83%
ISOXAZOLE
288-14-2

ISOXAZOLE

1-chloro-4-(3-methoxyhexa-4,5-dien-1-yn-1-yl)benzene

1-chloro-4-(3-methoxyhexa-4,5-dien-1-yn-1-yl)benzene

C15H10ClNO

C15H10ClNO

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 24h;83%
ISOXAZOLE
288-14-2

ISOXAZOLE

(Z)-p-chlorobenzaldehyde oxime
3717-23-5

(Z)-p-chlorobenzaldehyde oxime

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

phenylacetylene
536-74-3

phenylacetylene

3-(4-chlorophenyl)-4-phenylisoxazole
130966-62-0

3-(4-chlorophenyl)-4-phenylisoxazole

Conditions
ConditionsYield
With chloroamine-T In methanol; water82%
ISOXAZOLE
288-14-2

ISOXAZOLE

(S)-tert-butyl 2-((5-ethynylpyridin-3-yloxy)methyl)azetidine-1-carboxylate
1222139-46-9

(S)-tert-butyl 2-((5-ethynylpyridin-3-yloxy)methyl)azetidine-1-carboxylate

2-(2-nitroethoxy)tetrahydro-2H-pyran
75233-61-3

2-(2-nitroethoxy)tetrahydro-2H-pyran

3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-[3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-5-isoxazolyl]pyridine
1222139-58-3

3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-[3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-5-isoxazolyl]pyridine

Conditions
ConditionsYield
With phenyl isocyanate; triethylamine In hexane; benzene at 60℃; for 24h;82%
ISOXAZOLE
288-14-2

ISOXAZOLE

1-(tert-butyl)-4-(3-methoxyhexa-4,5-dien-1-yn-1-yl)benzene

1-(tert-butyl)-4-(3-methoxyhexa-4,5-dien-1-yn-1-yl)benzene

C19H19NO

C19H19NO

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 23h;82%
ISOXAZOLE
288-14-2

ISOXAZOLE

carbon dioxide
124-38-9

carbon dioxide

methyl iodide
74-88-4

methyl iodide

methyl 1,2-oxazole-5-carboxylate
15055-81-9

methyl 1,2-oxazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: carbon dioxide With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide In tetrahydrofuran at 20℃; under 1125.11 Torr; for 0.25h;
Stage #2: ISOXAZOLE In tetrahydrofuran at 20℃; under 1125.11 Torr; for 12h;
Stage #3: methyl iodide In tetrahydrofuran regioselective reaction;
81%
ISOXAZOLE
288-14-2

ISOXAZOLE

C12H18O

C12H18O

C14H17NO

C14H17NO

Conditions
ConditionsYield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver(I) triflimide In 1,2-dichloro-ethane at 65℃; for 33h;81%
ISOXAZOLE
288-14-2

ISOXAZOLE

titanium tetrachloride
7550-45-0

titanium tetrachloride

TiCl4(C3H3NO)2
161645-55-2

TiCl4(C3H3NO)2

Conditions
ConditionsYield
In benzene (N2); stirring; filtn., washing (benzene), drying (vac.); elem. anal.;80%

288-14-2Relevant articles and documents

-

Pouchan et al.

, p. 39,40,42,43 (1976)

-

Photocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: Cycloaddition reactivity and stability studies

Griesbeck, Axel G.,Franke, Marco,Neudoerfl, Joerg,Kotaka, Hidehiro

experimental part, p. 127 - 134 (2011/05/16)

The first photocycloadditions of aromatic and aliphatic aldehydes to methylated isoxazoles are reported. The reactions lead solely to the exo-adducts with high regio- and diastereoselectivities. Ring methylation of the isoxazole substrates is crucial for high conversions and product stability. The 6-arylated bicyclic oxetanes 9a-9c were characterized by X-ray structure analyses and showed the highest thermal stabilities. All oxetanes formed from isoxazoles were highly acid-sensitive and also thermally unstable. Cleavage to the original substrates is dominant and the isoxazole derived oxetanes show type T photochromism.

NOVEL FLORFENICOL-TYPE ANTIBIOTICS

-

, (2008/06/13)

The present invention relates to novel florfenicol compounds having the chemical structure: wherein the compounds are useful for the treatment and/or prevention of bacterial infections in a broad range of patients such as, without limitation, birds, fish, shellfish and mammals

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